Journal
NATURE CHEMISTRY
Volume 2, Issue 11, Pages 972-976Publisher
NATURE PUBLISHING GROUP
DOI: 10.1038/NCHEM.801
Keywords
-
Categories
Funding
- JSPS
- JST
Ask authors/readers for more resources
Asymmetric reactions that transform racemic mixtures into enantio-enriched products are in high demand, but classical kinetic resolution produces enantiopure compounds in <50% yield even in an ideal case. Many deracemization processes have thus been developed including dynamic kinetic resolution and dynamic kinetic asymmetric transformation, which can provide enantio-enriched products even after complete conversion of the racemic starting materials. However, these dynamic processes require racemization or symmetrization of the substrates or intermediates. We demonstrate a direct chemical enantio-convergent transformation without a racemization or symmetrization process. Copper(I)-catalysed asymmetric allylic substitution of a racemic allylic ether afforded a single enantiomer of an a-chiral allylboronate with complete conversion and high enantioselectivity (up to 98% enantiomeric excess). One enantiomer of the substrate undergoes an anti-S(N)2'-type reaction whereas the other enantiomer reacts via a syn-S(N)2' pathway. The products, which cannot be prepared by dynamic procedures, have been used to construct all-carbon quaternary stereocentres.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available